Dye of the anthraquinone series and process of making same.



UNITED STATES PATENT OFFICE.

ROLAND HEINRICH SCHOLL, or KARLSRUHE, GERMANY, ASSIGNOR "r BADISCHEANILIN & SODA FABR 1K, or LUDWIGSHAFEN-ON-THE-RHIN E,GERMANY,ACORPORAIION or BADEN.

DYE OF THE ANTHRAQUINONE SEBlES AND PROCESS OF MAKlNG SAME.

No. 856,811. Specification of Letters Patent. Patented June 11, 1907.

Application filed February 6, 1908. Serial No. 299.775.

Tom/l whom it may (OIL/515171,. I. The coloring matter whi h I desire toBe it known that I, ROLAND HEINRICH 1 claim specifically is thatobtainable from SCIIOLL, professor of che nistry and doctor of l 2.2-dimethyl 1.1 dianthraquinony philosophy, a subject of he King ofPrussia itself. it is abrown powder and yields orange and Grand Duke ofBaden, residing at Karlsshades on vegetable fiber. wish further to ruhe,in tho GramlDuchy of Baden, German be understood as claiming thesecoloring Empire, have invented new and useful lmmatters both bythemselves and also when provements in New Dyes ot" the Anthraquifixedon the fiber. They can be stripped none Series and Processes forProducing the from the fiber bymeansol' alkaline reducing 0 Same, ofwhich the following is a specilicaagents and can then be made to showthe tion. afore mentioned characteristic reactions.

In the specification of United States Lct- The following examples willserve to furters Patent No. 828,778, dated August 4, thcrillustratethcnature of my invention and 1906, I have described the production of athe method of carrying it into practical ef- 5 new clue. of compounds ofthe anthraquinone feet, but the invention is not confined to theseseries by heating a halogen anthramunone examples. The parts are byweight.

with a metal. such as copper, which has the Example 1. lleat togetherfor from one (1) 7c power of withdrawing halogen, and we have to two (2)hours, in a reflux apparatus, one termed these new bodiesdianthraquiuonyl (1) part of 'lfil -dimcthyl l.ldianthracompounds. Ihave now discovered that quinonyl with fifteen (15) parts ofpowdercd2.2"dimethyl1.1-'-dianthrmpiiuonyl on potassium hydrate and live (.5)parts of being heated either alone or with a condensmethyl alcohol in anoil-bath which is maining agent can be converted into coloring mattaincdat a temperature of from one hundred tor which upon reduction with analkaline and sixty-five (165 to one hundred and sevrcducing agent yieldsa rod vat which yes enty (l 70) degrees cenligrade, and then treat"egctablc'libcrrcd shades, whichshades upon the melt with water, inwhich it is soluble, washing become from orange to yellow and forming acarmine red solution. Boil the soare then entrcmcly fast. Instead of 232lution and pass airthrough it untilthe browndimctl'iyl"1.ldianthraquinonyl itself, its colorof the preci )itatcwhich forms no longer derivatives such for instance as its dichloralters. Then ma e slightlyacid,liltero'll', and its 4. l" dimcthylderivative can be cmwash. ploycd in carrying out my invention and I in-Exam le 2. Introduce one (1) part of 2,2- cludc all these compoundsunder the term a dimcthyl l .l-dianthraquinonyl into a 2.2 dimethyl V1.1. 'dianthraquinonyl mixture of three (3) parts of caustic )otashbody. The c loring matters obtained from and two and tlucciifths (2.6)parts oi ethyl those derivatives possess the same general alcohol andheat, while stirring. Maintain charactcristics as those of the coloringmatthe reaction mixture for from two (2) to ter obtained from the parentcompound. three. (25) hours at a temperature of from one As comlensingagent I have found alcoholic hundred and forty (140) to one. hundred andpotash to be very suitable, but other agents forty-five (145) degreesccutigradc. Treat may be employed, such for instance aszinc the meltwith hot water and )ass air tln'ough chlorid. the boiling liquid untilthe coior. of the. brown Tho coloring matters which desire toprecipitate no longer changes. Thcn filter claim generically consist offrom yellow to and wash with hot. water. instead of pro- ;5 brownpowders which are insoluble in water cccding in this manner, thedianthraquinonyl and in dilute acids and alkalics. They are com ound canbe boilcd with thirty (30) soluble in concentralml sulfuric. acidyielding times its weightof fifty (50) per cent. aqueous blue solutionsand are also soluble in hot nicaustic potash, or it can be melted at atrim tro-bcnzencand in hot anilin. 'lhcyarc solperature. of from twohundred and twenty 30" ublo inTilkalinehydrosulfitoyieldingredsolu-(221)) to two hundred and lift (250) degrees tions which yield onvegetable. libcr rod ccntigradc with a mixture of from tcu .(IU)

shades which shadeson washing bccomc from to fifteen (15) parts of solidcaustic polasit yellow to orange. and one (1) part of anhydrous sodiumacc- I acids and dilute alkilies.

tate. matter is obtained.

Example 3. Heat one (1) part of 2.2-di-- is at first greenish browngradually assumes a red-bron';'n color. After half an hour (30 minutes)allow the melt to cool and dissolve the mass obtained in from ten tofifteen parts of ninety-six (96) per cent. sulfuric acid. Precipitate bymeans of ice and water, iilter and wash with water. The compoundobtained is insoluble in water and in dilute It dissolves in ninety-six(96) per cent. sulfuric acid yielding a blue solution, and in hotnitrobenzene and in hot anilin yielding yellowish brown' v a temperatureoi" about two hundred and eighty (280) degrees centigrade, whereuponhydrochloric acid is evolved. A blood-red thick lluid melt is obtained,maintain this at the same temperature for about fifteen (15) minutes,and, after cooling, treat with warm water to which a little hydrochloridacid has been added, lilter and wash with hot water.

Example 5. introduce four (4},parts of i.4'*dichlor-2.2dimethyll.1dianthrai' uinonyl into a solution of thirty (30) parts of causticpotasli in thirty-tour (34) )arts of alcohol, and boil the whole gentlylor from one and a half (1.5) to two (2) hours in an oil-bath at atemperature of from one hundred and "titty (150) to one hundred andsixty (1.60) degrees centigrade. Allow the melt to cool, treat it withhot water, boil, and

pass air through the boiling solution until the brown color of the preciitate no longer clianges. Acidity, filter ant wash with hot water.

Example 6. Boil together, in a reflux apparatus, for three (23) hours,one (1) art of 2.2*4.4 tetramethyl l.1diant u'aquinonyl (prepared asdescribed in Example 50f the specification of United States LettersPatent No. 828,778, dated August 4,1906) and thirty 30) parts of asolution of caustic potash and. alcohol, of such strength that it boilsat a temperature of one hundred and In all these cases the same coloringthirty-five 135) degrees centigrade. Pour the reaction product intothree hundred (300) parts of water and ass air through the boilingliquid until the 'quid, which is at first red, becomes colorless and thereaction product has so arated out in yellowish red flakes. Then ter andwash with hot water.

Now what I claim is:

1. The process for the production of anthraquinone coloring matter byheating a 2.2dimethyl1.1dianthraquinony body. 1

2. The process for the production of'an- I thraquinone coloring matterby heatin a 2.2- dimethyl 1.1 dianthraquinony body with a condensingagent.

3. The process for the production of anthraquinone coloring matter byheati a 2.2- dimethyl 1.1 dianthraquino1i;% body with alcoholic potash.

4. The process for the production of anthraquinone coloring matter byheating 2.2-' dime thyl-l 1di anthraquinonyl with alcoholic potash.

5. As new articles of manufacture the anthraquinone coloring matterswhich can be obtained by heating a 2.2-dimethyl- 1.1-dianthrrquinonylbody with a condensing agent, which coloring matters consist of fromyellow to brown powders, which are in soluble in water and m diluteacids and in d lute alkalies, and are solublein "concentrated sulfuricacid yielding blue solutions and in hot nitrobenzene and in hot anilin,and which are also soluble in alkaline hydrosulfite yielding red vats,which yield red washing become from yellow to orange.

6. As a new article of manufacture the coloring'matter which can beobtained from 2.2 dimethyl 1.1 dianthraquinon 1, which colorin matter isa brown pow er which is insolu 1c in water and in dilute acids; and indilute alkalies, and is soluble incohcentrated sulfuric acid yielding ablue solution and in hot nitrobenzene, and s soluble in alkalinehydrosulfite' yielding a red vat which yields red shades on Vegetablefiber, which shades on washing become orange. 1

In testimony whereof I have hereunto set my hand in the witnesses. I

ROLAND HEINRICH SCHOLLF- Witnesses:

J. Arno. LLOYD, Jos. H. LEUTE.

shades on vegetable fiber, which shades on presence of two subscribing

